SYNTHESIS OF SULTAMS BY CYCLOALKYLATION OF (ALKOXYCARBONYLMETHANE)SULFONANILIDES

Authors

  • В. А. Рассадин Saint Petersburg University, Saint Petersburg 198504
  • А. А. Томашевский Saint Petersburg University, Saint Petersburg 198504
  • В. В. Соколов Saint Petersburg University, Saint Petersburg 198504
  • А. А. Потехин Saint Petersburg University, Saint Petersburg 198504

DOI:

https://doi.org/10.1007/7045

Keywords:

(methoxycarbonylmethane)sulfonanilides, sultams, cyclopropanes, heterocyclization

Abstract

(Methoxycarbonylmethane)sulfonanilides are alkylated by  α,ω-dihaloalkanes in K2CO3–DMF with the formation of sultams. A high sensitivity has been detected for the reaction rate on the electronic effect of substituents in the aromatic nucleus, although substituents in the  ortho  position  do not obstruct the reaction and in the case of 2,6-disubstituted derivatives the reaction rate and sultam yield were maximal. Tertiary sulfonamides form derivatives of 1-sulfamoylcyclopropanecarboxylic acid under these conditions.

How to Cite
Rassadin, V. A.; Tomashevskii, A. A.; Sokolov, V. V.; Potekhin, A. A..  Chem. Heterocycl. Compd. 2008, 44, 1. [Khim. Geterotsikl. Soedin. 2008, 1.]

For this article in the English edition see DOI 10.1007/s10593-008-0066-9


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Published

2022-09-14

Issue

No. 4 (2008)

Section

Original Papers